My sister dated “Pete” for three years. We all figured they would get married and were pretty surprised and frankly upset when we learned the relationship had ended. We all grew very close to him during the time they were together and considered him part of the family.

My sister is fairly private and didn’t go into deep details on the reasons, and not long after they broke up, Pete asked to meet for a drink. I did so, and did not tell my sister – he sounded very upset and it felt like the right thing to do. Pete was pretty upset about the breakup and while he said he wanted to respect my sister’s privacy, he did tell me that the breakup was her decision and he had asked her to consider counseling and had seen her as someone he could marry.

I haven’t seen Pete since that happened, but he continues to text and send messages that are almost always about my sister and how he wants to think of some way to get her back. I know enough from talking to her that isn’t going to happen but he just doesn’t want to hear that. He asks me things like whether she is seeing someone new (to my knowledge, she isn’t, but I haven’t said either way). I feel like I’m in a very awkward position now, but I’m not sure how to stop my friendship with Pete, even though I feel like if my sister knew this was going on, she’d feel betrayed. Advice?

Wanda says:

Advice: put family first. Advice: don’t get in the middle of drama between people you care about. Advice: cease and desist chatting with Pete. And that about sums it up.

Look, blood is thicker than water, no one knows what goes on in a relationship besides the two people in it, blah blah blah – clichés, but all true. Your sister is your sis for life, and there’s fair statistical data to assume that she could have many long relationships followed by subsequent break-ups before she ever gets married, and that’s if she gets married. What are you going to do, be BFF with every ex-BF in her wake and play counselor to their heartbreak? Not only is this completely inappropriate, but yes, it is a betrayal to your sister. There’s no clearer way to say it. She’s your sister; she wins!

Pete’s really taking advantage of your sympathies and sincerity and likely just sees you as a potential inroad back into your sister’s good graces. Doesn’t he have real friends he can confer with? Like, people he was friends with more than three years ago, before your sister? He doesn’t need to be engaged in clandestine conferences with you; he needs to get it through his head that sister’s not coming back and it’s time to move on already.

So do yourself a favor, and tell Pete you wish him well, but it’s high time to leave well enough alone and stop the sneaky sideline sessions before your sis finds out and has her heart broken all over again.

Wayne says:

Oh for Pete’s sake, tell the guy to keep you out of it. If he wants to drag this out or work to get her back, that’s on him – not you.

As Wanda wisely noted, your allegiances should be with your sister, now and forever. And she’s made it clear there’s no repeat performance for Pete. Maybe he’s needy and/or manipulative – seems to be working on you. Maybe he’s a jerk. Maybe he’s a dud. Maybe your sister just can’t see herself with him in 10 years with kids.

Here’s an idea: Why don’t you sit her down and ask her what happened? She’s private, sure, but she’s also your sister. This is a great opportunity to strengthen your friendship with her instead of with her now-ex-and-probably-forever-ex boyfriend who will also be an afterthought for you in about six months.

Breakups can be difficult and confusing, especially for a dumpee. But don’t join Pete in a state of denial or in a quirky Hallmark Channel movie plot – or worse, a devious Lifetime movie plot! – to get them back together. Cut the cable and cut the cord – let Pete go it alone.